Biomass-derived monomers for performance-differentiated fiber reinforced polymer composites

Rorrer, Nicholas A.; Vardon, Derek R.; Dorgan, John R.; Gjersing, Erica J.; Beckham, Gregg T.

doi:10.1039/C7GC00320J

Biomass-derived monomers for performance-differentiated fiber reinforced polymer composites

Journal Article · Tue Mar 14 00:00:00 EDT 2017 · Green Chemistry

DOI:https://doi.org/10.1039/C7GC00320J· OSTI ID:1369120

Rorrer, Nicholas A. ^[1]; Vardon, Derek R. ^[1]; Dorgan, John R. ^[2]; Gjersing, Erica J. ^[1]; ^[1]

National Renewable Energy Lab. (NREL), Golden, CO (United States)
Michigan State Univ., East Lansing, MI (United States)

Nearly all polymer resins used to manufacture critically important fiber reinforced polymer (FRP) composites are petroleum sourced. In particular, unsaturated polyesters (UPEs) are widely used as matrix materials and are often based on maleic anhydride, a four-carbon, unsaturated diacid. Typically, maleic anhydride is added as a reactant in a conventional step-growth polymerization to incorporate unsaturation throughout the backbone of the UPE, which is then dissolved in a reactive diluent (styrene is widely used) infused into a fiber mat and cross-linked. Despite widespread historical use, styrene has come under scrutiny due to environmental and health concerns; in addition, many conceivable UPEs are not soluble in styrene. In this study, we demonstrate that renewably-sourced monomers offer the ability to overcome these issues and improve overall composite performance. The properties of poly(butylene succinate)-based UPEs incorporating maleic anhydride are used as a baseline for comparison against UPEs derived from fumaric acid, cis,cis-muconate, and trans,trans-muconate, all of which can be obtained biologically. The resulting biobased UPEs are combined with styrene, methacrylic acid, or a mixture of methacrylic acid and cinnaminic acid, infused into woven fiberglass and cross-linked with the addition of a free-radical initiator and heat. This process produces a series of partially or fully bio-derived composites. Overall, the muconate-containing UPE systems exhibit a more favorable property suite than the maleic anhydride and fumaric acid counterparts. In all cases at the same olefinic monomer loading, the trans,trans-muconate polymers exhibit the highest shear modulus, storage modulus, and glass transition temperature indicating stronger and more thermally resistant materials. They also exhibit the lowest loss modulus indicating a greater adhesion to the glass fibers. The use of a mixture of methacrylic and cinnaminic acid as the reactive diluent results in a FRP composite with properties that can be matched to reinforced composites prepared with styrene. Significantly, at one-third the monomer loading (corresponding to two-thirds the number of double bonds), trans,trans-muconate produces approximately the same storage modulus and glass transition temperature as maleic anhydride, while exhibiting a superior loss modulus. Altogether, this work demonstrates the novel synthesis of performance-differentiated FRP composites using renewably-sourced monomers.

View Accepted Manuscript (DOE)

Research Organization:: National Renewable Energy Lab. (NREL), Golden, CO (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE), Bioenergy Technologies Office (EE-3B); USDOE Office of Energy Efficiency and Renewable Energy (EERE), NREL Laboratory Directed Research and Development (LDRD)

Grant/Contract Number:: AC36-08GO28308

OSTI ID:: 1369120

Report Number(s):: NREL/JA--5100-68265

Journal Information:: Green Chemistry, Journal Name: Green Chemistry Journal Issue: 12 Vol. 19; ISSN GRCHFJ; ISSN 1463-9262

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
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Biomass-derived monomers for performance-differentiated fiber reinforced polymer composites

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